Discover Your Perfect Hillside Vacation Homes

Hillside Pet Friendly Vacation Rentals

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9.2 (1017 Reviews)
Hotel
Heathman Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
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Hillside Large Vacation Homes

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Why Choose Rent By Owner for your Hillside Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for Hillside Vacation Rentals

Where are the best neighborhoods to stay in Hillside?

When choosing a neighborhood to stay in Hillside, Portland, Oregon, you’ll find an inviting mix of scenic views and peaceful surroundings that make for a perfect getaway. This area offers convenient access to local parks and charming streets, ideal for exploring on foot or bike. Whether you're seeking a quiet retreat or a vibrant community vibe, Hillside's neighborhood character provides a comfortable and authentic Portland experience that complements your stay. With a variety of well-maintained vacation rentals available, you'll be able to find the ideal place to unwind while enjoying the natural beauty and unique charm of this neighborhood.

Northwest Portland

This vibrant neighborhood offers a blend of cultural attractions and bustling streets, making it an ideal base for exploring the area's diverse neighborhoods. Staying here puts you close to many amenities and local favorite spots.

View 246+ Rentals in Northwest Portland

Alphabet Historic District

Known for its charming historic architecture, this district provides a cozy yet lively atmosphere for your stay in the region. It's perfect for visitors seeking a neighborhood with character and easy access to downtown Portland.

View 119+ Rentals in Alphabet Historic District

Nob Hill

Upscale and walkable, Nob Hill is renowned for its boutique shops and fine dining options, making it a desirable location for those wanting a stylish and convenient stay. The area's vibrant community adds to its appeal.

View 119+ Rentals in Nob Hill

Goose Hollow

This centrally located neighborhood combines historic charm with modern amenities, offering quick access to major attractions and public transportation. It’s an excellent choice for travelers who value accessibility.

View 87+ Rentals in Goose Hollow

Kings Heights

Perched atop a scenic hillside, Kings Heights provides panoramic views of the city and peaceful surroundings, appealing to visitors looking for a quiet yet picturesque spot to stay.

View 1069+ Rentals in Kings Heights

Arlington Heights

A residential area with tree-lined streets and scenic vistas, Arlington Heights offers a calm retreat within reach of Portland's main attractions. It suits guests seeking comfort in a tranquil environment.

View 1014+ Rentals in Arlington Heights

Willamette Heights

Situated above the Willamette River, this neighborhood features stunning views and lush greenery, providing a serene setting for your visit while maintaining close proximity to the city's core.

View 48+ Rentals in Willamette Heights

Sylvan-Highlands

Nestled among forested hills, Sylvan-Highlands offers a peaceful escape with scenic trails and natural beauty, ideal for travelers seeking outdoor activities combined with urban convenience.

View 837+ Rentals in Sylvan-Highlands

Best Times to Visit Hillside

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit here can enhance your experience, as the region offers distinct advantages depending on the season, ensuring you find the perfect moment for your relaxing getaway.

Peak Season Highlights

summer
Late Spring to Early Summer (May to June)

During this time, the region experiences warm weather ideal for enjoying outdoor activities and exploring local scenery.

Average Temperature Daytime: 70°F to 80°F - Nighttime: 50°F to 60°F
autumn
Early Fall (September to October)

This period offers mild temperatures and fewer tourists, making it perfect for a relaxed visit while still enjoying pleasant weather.

Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F

Off-Season Highlights

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Winter (December to February)

Cold temperatures and occasional rain characterize this season, providing a quiet time for peaceful stays in cozy rentals.

Average Temperature Daytime: 45°F to 55°F - Nighttime: 35°F to 45°F
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Late Fall (November)

As the region transitions into winter, lower visitor numbers make it an ideal time to find more affordable and tranquil accommodation options.

Average Temperature Daytime: 50°F to 60°F - Nighttime: 40°F to 50°F

Weekly Weather Forecast for Hillside

How to Book Your Hillside Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Hillside

More Top-Rated Vacation Rentals in Hillside Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy a spacious outdoor patio or deck perfect for relaxing and entertaining.
  • Take advantage of lush, landscaped gardens that add to the area's natural beauty.
  • Make use of convenient outdoor grilling facilities for barbecues and cookouts.
  • Benefit from private or shared yards ideal for outdoor activities or family gatherings.
  • Experience scenic views of the surrounding hills and greenery right from your rental.
  • Utilize dedicated outdoor seating areas to unwind after exploring the region.
  • Access nearby parks or trails for outdoor recreation and enjoying the fresh air.

Top Attractions Around Hillside

What attractions are nearby?

Here, you can explore a variety of outdoor activities, local parks, and cultural attractions that showcase the vibrant spirit of the region, making your stay both enjoyable and memorable.

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Family Activities

  • Portland Children's Museum: Engage your family with hands-on exhibits and interactive play areas designed to spark creativity and curiosity in young visitors.
  • Oregon Zoo: Explore the region’s most popular zoo, home to a diverse collection of animals and educational programs suitable for all ages.
  • Hoyt Arboretum: Enjoy scenic walking trails and discover a variety of native and exotic plant species amidst lush greenery ideal for family outings.
  • Pittock Mansion: Visit this historic estate offering panoramic views of the area along with engaging tours that bring Portland’s history to life for the entire family.
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Adult Activities

  • Explore Portland Art Museum: Immerse yourself in the region’s rich cultural scene by visiting the Portland Art Museum, located just a short drive from your Hillside vacation rental.
  • Enjoy a Stroll at Washington Park: Spend your day wandering through Washington Park to experience lush gardens, scenic walking paths, and spectacular city views here in Portland.
  • Savor Local Flavors at a Neighborhood Brewery: Taste craft beers at one of Portland's renowned breweries nearby, perfect for relaxing evenings in this vibrant destination.
  • Hike in Forest Park: Venture into Forest Park, one of the largest urban forests in the United States, offering miles of trails and natural beauty close to your Portland-area stay.

Other Places to Stay in Hillside, OR

Hillside Park Community Center
Hillside Park Community Center Vacation Rentals
Kings Heights
Kings Heights Vacation Rentals
Pittock Mansion
Pittock Mansion Vacation Rentals
More Places to Stay Near Hillside

Hillside Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Eateries: Take advantage of the area's renowned dining scene by visiting nearby cafes and farm-to-table restaurants to enjoy authentic regional flavors.
  • Plan Outdoor Activities: Utilize the natural beauty surrounding your vacation rental to hike, bike, or simply enjoy scenic walks that highlight the region's outdoor charm.
  • Visit Cultural Spots: Discover local art galleries, theaters, or historic sites in the area to immerse yourself in the region's vibrant cultural scene.
  • Optimize Your Stay with Local Events: Check out community calendars for festivals or markets that provide unique opportunities to experience the destination like a local.

Transportation Options

  • Light Rail Transit (MAX Light Rail): This efficient transit system connects you to key neighborhoods and the airport, making it easy to explore the region without a car when staying in Hillside.
  • Bus Services: Local bus routes provide convenient access throughout Portland and nearby areas, offering an affordable way to navigate the city from your rental here.
  • Rideshare Services: Popular options like Uber and Lyft operate seamlessly for quick, reliable rides around the area, ideal for those seeking flexibility during their stay.
  • Car Rentals: Several rental agencies are available locally, giving you the freedom to explore beyond the city at your own pace during your visit here.

Local Customs Options

  • Local Art Celebrations: You can experience the vibrant art scene with community festivals and gallery openings that highlight Portland’s creative spirit.
  • Farmers’ Market Traditions: Visiting the local farmers' markets allows you to enjoy fresh, seasonal produce and connect with regional growers and artisans.
  • Eco-Friendly Practices: The area's commitment to sustainability is evident through eco-conscious events and green initiatives embraced by residents and visitors alike.
  • Community Coffee Culture: Engaging in the popular coffeehouse gatherings offers a taste of Portland’s renowned caffeine scene and friendly neighborhood vibe.

Frequently Asked Questions About Hillside?

1. What are the top vacation rentals in Hillside?

There are a lot of options in Hillside. If you plan on staying in the Hillside area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Hillside:

2. How many vacation rentals have private pools in Hillside?

There are 14 vacation rentals with private pools near Hillside. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Hillside are best for families?

If you are looking for a family-friendly vacation home in Hillside, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Hillside:

4. How many Rentbyowner vacation rentals are available in Hillside?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 1228 in the Hillside area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Hillside. 

5. What is the cancellation policy for vacation rentals in Hillside, Portland?

Cancellation policies vary depending on the property owner’s terms. You should review the specific listing details or contact the host directly to understand the options available for your reservation.

6. How do I confirm my booking for a vacation rental in this area?

Booking confirmation typically occurs after you complete the reservation process and receive a confirmation email from the property owner or the platform. Ensure all required information is submitted correctly to secure your stay.

7. Are there any additional fees or deposits when booking here?

Additional fees such as cleaning fees, security deposits, or service charges may apply. These details are outlined in the listing, so be sure to review them carefully before confirming your reservation.

8. Can I modify or cancel my reservation if my plans change?

Modifications or cancellations depend on the property's policies. To ensure flexibility, read the cancellation and modification terms specified in the listing or contact the owner directly for assistance.

9. What amenities can I expect at vacation rentals in this region?

Amenities vary by property, but most rentals in this destination offer essentials like Wi-Fi, appliances, and parking. Check the specific listing for a comprehensive list of what is included during your stay.

Hillside Top Rated Vacation Rentals

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